Tottenham moved up to second in the Premier League but remain nine points behind Chelsea after drawing 0-0 at Sunderland on Tuesday night.

Mauricio Pochettino’s men went to the Stadium of Light in good form having lost just one of their previous nine league matches, but they struggled to break down a stubborn and resolute Sunderland backline, and had to settle for a share of the spoils.

Chelsea drew at Liverpool on the same night, so Spurs didn’t lose ground on Antonio Conte’s men, but you can’t help feel that they needed all three points to really keep the pressure on the league leaders.

Nonetheless, Pochettino’s side move above North London rivals Arsenal into second in the table after the Gunners lost at home to Watford, so Tottenham are well-placed to secure a second successive Champions League spot come May.

However, given that they were some way behind Chelsea going into January, many felt that Spurs needed to strengthen in the transfer market to try and bridge that gap, especially given that they were linked with many quality players during the window.

Yet, Spurs brought nobody in last month, and here are THREE massive deals that they missed out on…

Mahmoud Dahoud

Borussia Monchengladbach’s Mahmoud Dahoud has been a regular in the side ever since he made his debut for the club back in the 2014/15 season.

The German Under-21 international netted five goals and laid on nine assists in 32 league games last term to help the Bundesliga side to fourth place in the German top-flight.

His great form in the middle of the Monchengladbach midfield attracted interest from many top clubs around Europe, including Liverpool, last summer, yet he remained at the German outfit with it more likely that a move will take place at some stage this season.

Although he hasn’t been at his best this time round, making just 13 Bundesliga appearances thus far, Dahoud is still hot property, and the likes of Liverpool, Barcelona, and Tottenham were all reportedly keeping tabs on the youngster prior to the January window.

And he would have been an excellent signing for Tottenham, as he would have given them further depth to their midfield area, both for the present and indeed the future.

Ross Barkley

Ross Barkley struggled to impose himself on the Everton team for much of the first half of the season, although one of his three Premier League goals did come against Spurs on the opening day.

The England international was occasionally left out of match-day squads by Toffees boss Ronald Koeman, and as a result there was much speculation surrounding his future at Goodison Park.

One club reportedly interested in the 23-year-old was Tottenham, with Pochettino clearly possessing an excellent record of giving young players a chance, but also getting them to flourish in the first team.

It would have been a great move for Barkley, especially given what Pochettino has done for the likes of Harry Kane, Dele Alli, and Eric Dier, yet the Everton man has seen a remarkable upturn in form since the start of December, where he’s netted once and assisted three other times for the club.

Barkley’s improved displays and greater confidence looks set to keep him in the Toffees team for a while yet.

Isco

This was the deal that had many Tottenham fans excited over the January window, but it was one they were unable to get done.

Real Madrid’s Isco has been on the peripheries of the first team for much of the season, starting just nine of their 19 La Liga games thus far, as well as just one of their Champions League matches.

Despite netting four times and grabbing three assists in his time on the pitch this term, the 24-year-old isn’t any nearer to breaking into the side on a regular basis, and so there was speculation that he might leave the club last month.

And Spurs were heavily linked with the Spanish international, who would have added great depth and competition to an already-talented midfield department at White Hart Lane.

Although they didn’t get a deal done in January, if Isco continues to find first team opportunities hard to come by for the rest of the season, it wouldn’t be a surprise to see Spurs up their interest in the summer.